# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ldmlh180511
_database_code_depnum_ccdc_archive 'CCDC 1856447'
loop_
_audit_author_name
_audit_author_address
'Lydia Karmazin'
;Institut de Chimie de Strasbourg
France
;
_audit_update_record             
;
2018-07-17 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 N2, Br'
_chemical_formula_sum            'C21 H27 Br N2'
_chemical_formula_weight         387.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.7618(11)
_cell_length_b                   8.5269(3)
_cell_length_c                   14.2656(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.281(2)
_cell_angle_gamma                90
_cell_volume                     1999.25(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    41357
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68467
_exptl_absorpt_correction_T_max  0.84847
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34724
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_av_R_equivalents  0.1428
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.239
_diffrn_reflns_theta_max         27.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4527
_reflns_number_gt                2887
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+1.1054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.1675
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4547(3) 0.4569(6) 0.2866(4) 0.0329(11) Uani 1 1 d . . . . .
H1 H 0.4596 0.5605 0.2652 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4114(3) 0.2172(5) 0.2911(4) 0.0340(12) Uani 1 1 d . . . . .
H2 H 0.3802 0.1237 0.2726 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4777(3) 0.2400(5) 0.3759(4) 0.0341(12) Uani 1 1 d . . . . .
H3 H 0.5016 0.1662 0.4288 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3316(3) 0.3825(5) 0.1400(4) 0.0335(12) Uani 1 1 d . . . . .
C5 C 0.3499(3) 0.4143(6) 0.0572(4) 0.0404(13) Uani 1 1 d . . . . .
H5 H 0.4049 0.4196 0.0629 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2860(4) 0.4390(6) -0.0365(4) 0.0493(15) Uani 1 1 d . . . . .
H6 H 0.2981 0.4652 -0.0940 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2078(4) 0.4260(6) -0.0462(4) 0.0484(15) Uani 1 1 d . . . . .
H7 H 0.1657 0.4392 -0.1111 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1873(3) 0.3934(6) 0.0376(4) 0.0415(13) Uani 1 1 d . . . . .
C9 C 0.1053(4) 0.3813(7) 0.0299(5) 0.0571(16) Uani 1 1 d . . . . .
H9 H 0.0623 0.3912 -0.0344 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0880(4) 0.3559(8) 0.1127(5) 0.0631(18) Uani 1 1 d . . . . .
H10 H 0.0328 0.3472 0.1058 0.076 Uiso 1 1 calc R U . . .
C11 C 0.1501(3) 0.3421(7) 0.2090(5) 0.0532(15) Uani 1 1 d . . . . .
H11 H 0.1365 0.3272 0.2667 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2297(3) 0.3501(6) 0.2203(4) 0.0406(13) Uani 1 1 d . . . . .
H12 H 0.2713 0.3398 0.2857 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2506(3) 0.3739(5) 0.1345(4) 0.0369(12) Uani 1 1 d . . . . .
C14 C 0.5777(3) 0.4621(6) 0.4467(4) 0.0358(12) Uani 1 1 d . . . . .
H14A H 0.5776 0.4470 0.5155 0.043 Uiso 1 1 calc R U . . .
H14B H 0.5777 0.5763 0.4339 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6536(3) 0.3886(6) 0.4410(4) 0.0368(12) Uani 1 1 d . . . . .
H15A H 0.6536 0.2747 0.4545 0.044 Uiso 1 1 calc R U . . .
H15B H 0.6528 0.4022 0.3717 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7306(3) 0.4611(7) 0.5165(4) 0.0459(14) Uani 1 1 d . . . . .
H16A H 0.7318 0.4453 0.5858 0.055 Uiso 1 1 calc R U . . .
H16B H 0.7298 0.5754 0.5041 0.055 Uiso 1 1 calc R U . . .
C17 C 0.8079(3) 0.3910(7) 0.5101(4) 0.0479(14) Uani 1 1 d . . . . .
H17A H 0.8558 0.4370 0.5647 0.058 Uiso 1 1 calc R U . . .
H17B H 0.8084 0.2767 0.5226 0.058 Uiso 1 1 calc R U . . .
C18 C 0.8164(4) 0.4173(8) 0.4106(5) 0.0600(17) Uani 1 1 d . . . . .
H18A H 0.8172 0.5318 0.3992 0.072 Uiso 1 1 calc R U . . .
H18B H 0.7676 0.3742 0.3561 0.072 Uiso 1 1 calc R U . . .
C19 C 0.8910(4) 0.3457(8) 0.4012(5) 0.070(2) Uani 1 1 d . . . . .
H19A H 0.9402 0.3952 0.4514 0.084 Uiso 1 1 calc R U . . .
H19B H 0.8928 0.2324 0.4172 0.084 Uiso 1 1 calc R U . . .
C20 C 0.8922(5) 0.3657(11) 0.2966(7) 0.109(3) Uani 1 1 d . . . . .
H20A H 0.8417 0.3188 0.2473 0.131 Uiso 1 1 calc R U . . .
H20B H 0.8903 0.4794 0.2819 0.131 Uiso 1 1 calc R U . . .
C21 C 0.9613(5) 0.2986(12) 0.2777(7) 0.118(3) Uani 1 1 d . . . . .
H21A H 1.0123 0.3406 0.3272 0.177 Uiso 1 1 calc R U . . .
H21B H 0.9569 0.3261 0.2091 0.177 Uiso 1 1 calc R U . . .
H21C H 0.9609 0.1842 0.2843 0.177 Uiso 1 1 calc R U . . .
N1 N 0.3970(2) 0.3547(4) 0.2359(3) 0.0326(10) Uani 1 1 d . . . . .
N2 N 0.5043(2) 0.3909(4) 0.3717(3) 0.0310(9) Uani 1 1 d . . . . .
Br1 Br 0.41945(4) 0.82284(6) 0.35204(4) 0.0439(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.325(6) . ?
C1 N1 1.330(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.344(7) . ?
C2 N1 1.381(6) . ?
C2 H2 0.9500 . ?
C3 N2 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(7) . ?
C4 C13 1.413(7) . ?
C4 N1 1.439(6) . ?
C5 C6 1.403(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.347(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(8) . ?
C8 C13 1.423(7) . ?
C9 C10 1.346(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.422(7) . ?
C12 H12 0.9500 . ?
C14 N2 1.468(6) . ?
C14 C15 1.517(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.515(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.532(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.500(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.511(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.510(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.469(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 109.1(4) . . ?
N2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
C3 C2 N1 107.5(4) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 107.1(4) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C5 C4 C13 122.3(5) . . ?
C5 C4 N1 118.9(5) . . ?
C13 C4 N1 118.8(4) . . ?
C4 C5 C6 118.8(5) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.2(5) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 122.5(5) . . ?
C7 C8 C13 119.0(5) . . ?
C9 C8 C13 118.4(5) . . ?
C10 C9 C8 120.8(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 121.0(6) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.4(6) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C4 C13 C12 123.6(5) . . ?
C4 C13 C8 117.5(5) . . ?
C12 C13 C8 119.0(5) . . ?
N2 C14 C15 110.6(4) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 112.0(4) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 112.7(4) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 114.3(5) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 115.4(5) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 112.6(6) . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 117.6(7) . . ?
C21 C20 H20A 107.9 . . ?
C19 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
C19 C20 H20B 107.9 . . ?
H20A C20 H20B 107.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C2 107.9(4) . . ?
C1 N1 C4 125.9(4) . . ?
C2 N1 C4 126.2(4) . . ?
C1 N2 C3 108.4(4) . . ?
C1 N2 C14 126.2(4) . . ?
C3 N2 C14 125.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.8(5) . . . . ?
C13 C4 C5 C6 -0.1(7) . . . . ?
N1 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 C7 -2.5(7) . . . . ?
C5 C6 C7 C8 2.5(8) . . . . ?
C6 C7 C8 C9 179.1(5) . . . . ?
C6 C7 C8 C13 0.0(8) . . . . ?
C7 C8 C9 C10 -177.4(6) . . . . ?
C13 C8 C9 C10 1.7(9) . . . . ?
C8 C9 C10 C11 0.6(10) . . . . ?
C9 C10 C11 C12 -1.7(9) . . . . ?
C10 C11 C12 C13 0.5(8) . . . . ?
C5 C4 C13 C12 -176.2(5) . . . . ?
N1 C4 C13 C12 4.7(7) . . . . ?
C5 C4 C13 C8 2.5(7) . . . . ?
N1 C4 C13 C8 -176.6(4) . . . . ?
C11 C12 C13 C4 -179.6(5) . . . . ?
C11 C12 C13 C8 1.7(7) . . . . ?
C7 C8 C13 C4 -2.4(7) . . . . ?
C9 C8 C13 C4 178.4(5) . . . . ?
C7 C8 C13 C12 176.3(5) . . . . ?
C9 C8 C13 C12 -2.8(7) . . . . ?
N2 C14 C15 C16 179.2(4) . . . . ?
C14 C15 C16 C17 -178.6(4) . . . . ?
C15 C16 C17 C18 62.9(7) . . . . ?
C16 C17 C18 C19 -178.4(5) . . . . ?
C17 C18 C19 C20 175.5(7) . . . . ?
C18 C19 C20 C21 -179.1(8) . . . . ?
N2 C1 N1 C2 -0.7(5) . . . . ?
N2 C1 N1 C4 179.9(4) . . . . ?
C3 C2 N1 C1 0.9(5) . . . . ?
C3 C2 N1 C4 -179.6(4) . . . . ?
C5 C4 N1 C1 62.2(6) . . . . ?
C13 C4 N1 C1 -118.6(5) . . . . ?
C5 C4 N1 C2 -117.2(5) . . . . ?
C13 C4 N1 C2 62.0(6) . . . . ?
N1 C1 N2 C3 0.2(5) . . . . ?
N1 C1 N2 C14 177.3(4) . . . . ?
C2 C3 N2 C1 0.4(5) . . . . ?
C2 C3 N2 C14 -176.7(4) . . . . ?
C15 C14 N2 C1 -106.5(5) . . . . ?
C15 C14 N2 C3 70.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 Br1 0.95 2.78 3.383(5) 122.4 .
C2 H2 Br1 0.95 2.78 3.463(4) 129.1 1_545
C3 H3 Br1 0.95 2.90 3.648(5) 136.2 3_666
C5 H5 Br1 0.95 3.00 3.878(5) 154.0 2_645
C14 H14A Br1 0.99 2.97 3.747(5) 136.6 3_666
C15 H15B Br1 0.99 3.03 3.920(5) 149.9 2_645

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.123

